Hydrochloric Acid → N-[4-(4-Methoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

HRID 1417267ノート

反応式

HRID 1417267 の反応式
Br.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([NH:15][S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[S:13][CH:14]=2)=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 164648644-(4-Methoxy-phenyl)-thiazol-2-ylamine; hydrobromide

生成物 1

HCID 2400649N-[4-(4-Methoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide収率 38.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 0.5 g of 4-(4-methoxy-phenyl)-thiazol-2-ylamine hydrobromide with 0.37 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and the mixture was extracted twice with 40 ml of ethyl acetate each time. The organic phases were combined, dried with magnesium sulphate and the solvent was removed on a rotary evaporator. The residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.4 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 30 ml of 50% ethanol yielded 0.24 g of N-[4-(4-methoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as beige crystals.

後処理

  1. extractionthe mixture was extracted twice with 40 ml of ethyl acetate each time
  2. dry with materialdried with magnesium sulphate
  3. customthe solvent was removed on a rotary evaporator
  4. dissolutionThe residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  5. additionAfter the addition of 0.4 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customThe product separated upon neutralization with concentrated hydrochloric acid
  8. customRecrystallization from 30 ml of 50% ethanol

出典と根拠

ORDレコード
ord-2fce9626687340a5a24e699822a5567e
出典データセット
uspto-grants-1999_03
特許番号
US05877193

反応ノート

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